The Peak Season

Mike O'Connell built Happy Guest because the slick guest portals big property managers had weren't accessible to everyday hosts. He breaks down the full platform, why calling guests after they book is one of the highest-ROI moves in the business, and what their MCP launching next week unlocks. 🏠

http://www.happyguestofficial.co

Happy Guest is built around three pillars: pre-arrival requirements, a digital guidebook, and damage protection. The pricing is consumption-based, meaning they only make money when you make money. Mike and his co-founder Kane operate their own STR building in Fort Lauderdale, which gives them a real testing ground for every feature before it goes live.

The pre-arrival flow sends guests a custom URL via message or SMS immediately after booking. Inside, they sign a rental agreement, agree to house rules, and complete ID verification in one gamified journey. The friction is intentional. A guest who balks at signing a rental agreement is a red flag worth knowing about early, and the guidebook only unlocks after every requirement is complete.

The digital guidebook is scrollable and video-friendly, which matters more than it sounds. A short video showing how to use the door lock or the washing machine eliminates an entire category of guest messages. QR codes on appliances handle the rest. Mike also walks through exporting your full PMS message history into Claude and prompting it to surface the questions guests keep asking, which tells you exactly what to fix in your flow.

On the damage side, Happy Guest runs a marketplace of waiver carriers where hosts file a claim with a photo and a click. Claims pay out within days without involving the guest at all. Co-hosts can mark up the waiver cost per reservation and turn it into a recurring profit center. And because Happy Guest captures the guest's phone number and email at sign-up, hosts own that relationship in a way Airbnb no longer makes easy. Their MCP launches next week, connecting Claude directly to your Happy Guest account.

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🎁 LISTENER DEALS & RESOURCES

Try Hospitable, save $30 on your first month:

👉 http://hospitable.com/?grsf=lucas-7x7c6d

Google Workspace, 10% off for a full year:

👉 https://referworkspace.app.goo.gl/oBsX

Go High Level, 14-Day Free Trial:

👉 http://gohighlevel.com/?fp_ref=peakseason

PriceLabs, 30-Day Free Trial + $10 Credit:

👉 http://pricelabs.co/users/sign_up?referral=KxzeNH

Join The Connected Host Community, includes a GHL Sub Account:

👉 http://skool.com/the-connected-host-5639

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Disclaimer: The content in this episode is for educational and informational purposes only. Nothing discussed constitutes financial, legal, tax, or investment advice. Short-term rental regulations, platform policies, and tax laws vary by location and change frequently. Always verify what applies in your market. Results mentioned are not typical and are not a guarantee of your results. Luke, Tyler, and The Peak Season Podcast are not liable for decisions made based on information in this episode. Consult qualified professionals before taking action.

PC built Hospitable into the only PMS processing $60M+ in direct booking payments, and now he's giving the software away for free. He explains why, and walks through four moves reshaping how STR operators run their business: the industry's first MCP, a live VRBO integration, a free plan, and a marketplace matching owners to property managers.

🔌 HOSPITABLE'S MCP: WHAT IT ACTUALLY DOES

- First PMS in the STR industry to launch a Model Context Protocol integration

- A competitor followed within days; MCP is about to become table stakes for any serious tool

- Lets AI agents access Hospitable data: reservations, pricing, availability, messaging

- Buildathon campaign is running now in the community to drive adoption fast

📅 THE VRBO INTEGRATION

- Pilot launched March 2026; moving from batch updates to a real-time source-of-truth API

- Hospitable becomes merchant of record for Verbo direct bookings: taxes, chargebacks, payments handled

- Verbo guests pay through Hospitable's infrastructure, not a third-party processor

- Big for co-hosts: cleaner payout flow and no more double-booking risk

💳 THE FREE PLAN IS REAL

- Essentials plan is free forever with no property cap

- Revenue model shifts to performance: Hospitable earns on payments, not subscriptions

- "Software is dead. The value of it is going to zero. We're totally fine with it."

- The bet: own the payment layer and you don't need to charge for the tool

🏠 THE PROPERTY MANAGER MARKETPLACE

- Owners submit through the marketplace; vetted PMs get matched to the deal

- Live now, no fee to join, inbound deal flow available for co-hosts immediately

- Luke has used it and picked up real inquiries without cold outreach

- Built for operators who want leads, not more marketing work

🧠 HOW PC THINKS ABOUT THE NEXT 3 YEARS

- Hospitable is betting on becoming infrastructure, not just another software subscription

- The operator who understands the payment layer will have a structural advantage

- Open ecosystem: MCP means any AI agent can plug directly into your property data

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🎁 LISTENER DEALS & RESOURCES

Try Hospitable, save $30 on your first month:

👉 http://hospitable.com/?grsf=lucas-7x7c6d

Google Workspace, 10% off for a full year:

👉 https://referworkspace.app.goo.gl/oBsX

Go High Level, 14-Day Free Trial:

👉 http://gohighlevel.com/?fp_ref=peakseason

PriceLabs, 30-Day Free Trial + $10 Credit:

👉 http://pricelabs.co/users/sign_up?referral=KxzeNH

Join The Connected Host Community, includes a GHL Sub Account:

👉 http://skool.com/the-connected-host-5639

Disclaimer: The content in this episode is for educational and informational purposes only. Nothing discussed constitutes financial, legal, tax, or investment advice. Short-term rental regulations, platform policies, and tax laws vary by location and change frequently. Always verify what applies in your market. Results mentioned are not typical and are not a guarantee of your results. Luke, Tyler, and The Peak Season Podcast are not liable for decisions made based on information in this episode.

Brandon Pottebaum left college athletics after 10 years to go full-time in STRs, running 14 doors with one VA and a freelance revenue manager. No employees, no overhead, just a lean system built on smart tools and clear priorities. This week: how he built it, what he still does manually, and where AI is about to change his whole operation. 🎙️

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🧠 FROM W2 TO 14 DOORS

- Left football after co-hosting scaled faster than he could manage both

- Wife kept her W2, and the blend model provides stability while he builds

- Started in Blue Ridge in 2021, now owns 5 and co-hosts 9 across four markets

- Went full-time end of 2024 with kids 6 and 4 at home

👥 LEAN TEAM STRUCTURE

- One VA in the Philippines: listing ops, SOPs, upsell scripts, social media

- Freelance revenue manager works a W2 at a pricing tool; co-hosting is his side hustle

- Project-based, async. No daily check-ins, just a rolling task list

- Next hire will likely be someone to steer AI tools, not do manual work

🔌 HOSPITABLE VS. HOSTBUDDY

- HostBuddy earns its keep on late-night emergencies and repetitive Q&A

- Hospitable owns the scheduled message sequences. Don't mix them.

- Put your bio in HostBuddy's instructions or it will confidently say the wrong thing

- Both go rogue. Coach them hard up front, then trust but verify

📊 FACEBOOK > INSTAGRAM FOR DIRECT BOOKINGS

- Organic Instagram is for owner credibility, not guest bookings

- Facebook group activity drives real direct booking traffic

- LinkedIn is purely for owners, investors, and co-hosting partnerships

- Three platforms, three strategies, three different goals

🛠️ CLAUDE IN THE REAL WORLD

- One CSV from PriceLabs now updates his entire 10-property revenue spreadsheet

- Rankings tracking: Claude opens incognito, searches Airbnb, returns rank in seconds

- Goal: cleaners flag low supplies in Slack, Claude adds to Amazon cart by property

- Start with your biggest pain point and teach the tool to solve exactly that

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🎁 LISTENER DEALS & RESOURCES

Try Hospitable, save $30 on your first month:

👉 http://hospitable.com/?grsf=lucas-7x7c6d

Google Workspace, 10% off for a full year:

👉 https://referworkspace.app.goo.gl/oBsX

Go High Level, 14-Day Free Trial:

👉 http://gohighlevel.com/?fp_ref=peakseason

PriceLabs, 30-Day Free Trial + $10 Credit:

👉 http://pricelabs.co/users/sign_up?referral=KxzeNH

Join The Connected Host Community, includes a GHL Sub Account:

👉 http://skool.com/the-connected-host-5639

---

Disclaimer: The content in this episode is for educational and informational purposes only. Nothing discussed constitutes financial, legal, tax, or investment advice. Short-term rental regulations, platform policies, and tax laws vary by location and change frequently. Always verify what applies in your market. Results mentioned are not typical and are not a guarantee of your results. Luke, Tyler, and The Peak Season Podcast are not liable for decisions made based on information in this episode. Consult qualified professionals before taking action.

Your calendar is your inventory. When a guest cancels a premium week, how you respond affects your rebooking odds, your Airbnb ranking, and sometimes your review score. Luke and Tyler break down every cancellation scenario — last-minute, weather-related, peak season, and the one move Luke will never make no matter what the guest says. 🏔️

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📅 DYNAMIC CANCELLATION POLICIES
Airbnb now lets you set different policies at different times of year. Stricter in peak, more flexible in the shoulder. New listings: start liberal to build algorithm traction, then tighten as reviews come in.

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⚖️ BEND OR HOLD FIRM
How close is check-in? A next-weekend cancel gets held. Four months before summer gets flexibility — you'll likely rebook higher. Read it: genuine emergency, or someone chasing a better deal?

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❌ NEVER LET THEM RESCHEDULE
Luke will not allow a cancel-and-rebook. They'll reschedule outside your cancellation window, then cancel penalty-free. Dynamic pricing means they'll expect the same rate — they won't get it. Full refund, partial, or no refund. Nothing in between.

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🌧️ WEATHER CANCELLATIONS
Actual travel advisory? Approve it. "It might rain" is a preference, not an emergency. Remind guests the reservation covers the blocked calendar, not just time on property. Offer: if I can rebook those dates, I'll refund what I recover.

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🔱 THE CANCELLATION TRIDENT
Step 1 — Hear them out. Understand the actual situation.
Step 2 — Explain the calendar block. You lost bookings the moment they confirmed.
Step 3 — Offer the rebook exception. Dates fill, you refund what you recover.

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✈️ TRAVEL INSURANCE
Guests are offered it at checkout — on platform and in your messaging. If they didn't buy it, that's their call. If they did, offer documentation help. Closes the conversation cleanly.

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📈 THE ALGORITHM PLAY
Approving a guest-requested cancel during peak season can trigger a ranking bump. Fewer restrictions — fees, deposits, strict policies — push you higher in Airbnb results.

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🎁 LISTENER DEALS & RESOURCES

Try Hospitable — Save $30 on your first month:
👉 http://hospitable.com/?grsf=lucas-7x7c6d

Google Workspace — 10% off for a full year:
👉 https://referworkspace.app.goo.gl/oBsX

Go High Level — 14-Day Free Trial:
👉 http://gohighlevel.com/?fp_ref=peakseason

PriceLabs — 30-Day Free Trial + $10 Credit:
👉 http://pricelabs.co/users/sign_up?referral=KxzeNH

Join The Connected Host Community — includes a GHL Sub Account:
👉 http://skool.com/the-connected-host-5639

---

Disclaimer: The content in this episode is for educational and informational purposes only. Nothing discussed constitutes financial, legal, tax, or investment advice. Short-term rental regulations, platform policies, and tax laws vary by location and change frequently — always verify what applies in your market. Results mentioned are not typical and are not a guarantee of your results. Luke, Tyler, and The Peak Season Podcast are not liable for decisions made based on information in this episode. Consult qualified professionals before taking action.

Big news for STR hosts — Hospitable just launched a full API integration with VRBO, and it changes everything. Luke and Tyler break down what the old (broken) connection looked like, what the new integration actually delivers, and whether it's finally worth getting back on VRBO. 🏠

Before: VRBO ran on a public API — tons of manual work, no automated guest messaging, constant calendar sync failures, and real double-booking risk.

Now: A true API handshake, just like Airbnb and Booking.com. Automated guest comms, real-time calendar and pricing sync, full listing management (photos, amenities, descriptions), and auto-listing creation — all from within Hospitable.

The headline feature: Hospitable now collects guest payments directly — no separate Stripe accounts needed. That unlocks:

• Chargeback protection — Hospitable fights disputes on your behalf
• Tax remittance — automated in all states except CA, NV, AK, MO & LA
• Seamless upsells — one-click early check-ins, late checkouts & more

Before After $1,000 booking VRBO keeps 8% → you get $920 VRBO 5% + Hospitable 3.9% → you get $911

That ~$9 difference buys chargeback protection and tax remittance. Worth it.

Tip: Bump your base rates to account for the new 8.9% total before this goes live.

Still new — Hospitable is running a pilot program to iron out bugs. Luke is testing with one listing and will report back in a follow-up episode.

Try Hospitable — Save $30 on your first month (this episode's sponsor): 👉 hospitable.com/?grsf=lucas-7x7c6d

Google Workspace — 10% off for a full year: 👉 Get the deal

Go High Level — 14-Day Free Trial (the CRM Luke uses to run his business): 👉 gohighlevel.com/?fp_ref=peakseason

PriceLabs — 30-Day Free Trial + $10 Credit (dynamic pricing that pays for itself): 👉 pricelabs.co/users/sign_up?referral=KxzeNH

Join The Connected Host Community — includes a GHL Sub Account: 👉 skool.com/the-connected-host-5639

Disclaimer: The content shared in this episode is for educational and informational purposes only and does not constitute financial, legal, or investment advice. Peak Season Podcast and its hosts are not liable for any decisions made based on information presented here. Always consult qualified professionals before making real estate or investment decisions.

Guest: Andrea Moxham, Founder of Moxie & Co. | Hosts: Luke Miller & Tyler K.

Interior designer Andrea Moxham joins Luke and Tyler to break down the most common design mistakes STR hosts make when DIYing their properties — with actionable tips you can implement right away, no renovation required. Whether you're just getting started or you've got a full portfolio, this one's a must-listen! 🏡

About Andrea: Marketing background turned full-time STR interior designer. She designs 3–5 properties per month virtually, with install teams across the US handling on-site setup in 5–6 days.

1. Designing for Yourself (00:07:56) Hosts default to the safe neutrals they'd use at home. Instead, design for your guest avatar — think about who's actually booking and what experience they're seeking.

2. No Cohesive Theme Room-to-Room (00:13:08) Painting every room the same color blurs together in listing photos; clashing styles feel disjointed. Make each bedroom and bathroom look distinctly different so guests can grasp the full size of the property while scrolling.

3. Generic, Overused Art (00:16:16) Skip the mass-produced Highland Cow 🐄. Think beyond frames — hang maps, blankets, or locally inspired items. Ask: would a guest stop to photograph this or study it over morning coffee? Great sources: Etsy, eBay, and Fine Art America (fineartamerica.com) for location-specific prints.

4. Shallow Guest Avatar Research (00:24:34) "Families" isn't specific enough. Pull competitor reviews into ChatGPT, search Instagram for the location to see what visitors photograph, study tagged photos at competitor properties, and use Google Trends to understand where travelers are coming from.

5. Rug Mistakes (00:31:24) No rug — or a wrong-sized one — is Andrea's biggest pet peeve 😤. Rules of thumb: bedrooms need a minimum 8x10 with feet hitting the rug on any side; living rooms need front legs of all furniture on the rug; dining rooms benefit from an indoor/outdoor rug for easy cleanup. Budget: a couple hundred dollars max.

6. Missing Window Treatments (00:36:28) Curtains are the most affordable room upgrade you're probably skipping. Replace metal cellular blinds immediately — they date a space instantly. Hang rods at least 6 inches above the frame with curtains reaching the floor. Use fabric Roman shades where curtains won't fit.

• Furniture: ~$10,000 × number of bedrooms (e.g., 5BR = ~$50K)
• Designer fees: Typically $3–$20/sq ft depending on scope and market

• Instagram: @andreamoxham
• Website: moxieandco.ca
• Free Resources: moxieandco.ca/freebies

Disclaimer: The content shared in this episode is for educational and informational purposes only and does not constitute financial, legal, or investment advice. Peak Season Podcast and its hosts are not liable for any decisions made based on information presented here. Always consult qualified professionals before making real estate or investment decisions.

Your guidebook is one of the most powerful tools you have for delivering a 5-star guest experience. In this episode, Luke and Tyler break down what to put in it, how to deliver it, and which platform makes the most sense for where you are in your hosting journey.

(00:30) — What to Include Directions, local restaurants, attraction info, and specialty amenity instructions are the non-negotiables. Pro tip: record a YouTube Short for tricky things like a wood stove or geodome and link it right in the guide. Add a "Prepare for Your Adventure" section to set expectations upfront — fewer 11pm messages.

(03:26) — How to Deliver It Send the link at booking via Hospitable automations. Bonus: use your property domain (e.g. sevenpineschalet.com/guidebook) to naturally funnel guests back to your direct booking site — Airbnb can't scrub what's built into the URL itself.

(05:55) — Option 1: Physical Guidebook Still works, especially for older guests. Downside: updates require coordinating with your cleaner.

(08:49) — Option 2: Canva (Free) Build a guidebook doc, share via link. No subscription, easy to update, and AI tools like Claude or ChatGPT can now help you build one fast.

(11:24) — Option 3: TouchStay (~$99/year) Templated and reliable. Tyler's go-to. Getting better all the time with upsell features, video support, and regular updates.

(13:55) — Option 4: Happy Guest (Free for 10+ reservations/year) Builds the guidebook for you, including migrating from TouchStay. TikTok-style scroll interface. Also handles rental agreements, security deposits, guest insurance, and early check-in upsells.

(18:33) — Option 5: Custom Website Luke's setup — guidebooks as standalone pages in Go High Level. Full control, analytics, email capture, and no added cost. peakseasonpodcast.com was built the same way using Claude.

(20:41) — AI & What's Next "AI will teach you how to use AI." Next episode: AI goes head-to-head against TouchStay and Happy Guest using Tyler's real guidebook as the benchmark.

• TouchStay — touchstay.com | ~$99/year
• Happy Guest — happyguestofficial.com | Free for 10+ reservations/year
• Canva — canva.com
• Hospitable — hospitable.com
• Go High Level — gohighlevel.com
• Claude — claude.ai

📸 Instagram: @peakseasonpodcast 🌐 peakseasonpodcast.com

Like, subscribe, and share if this was helpful. See you on the next one. ☀️

Disclaimer: The content of The Peak Season Podcast is for informational and entertainment purposes only and does not constitute legal, financial, or professional advice. Pricing and features of tools mentioned are subject to change — verify directly with providers. Hosts may have affiliate relationships with products discussed. Always do your own due diligence.

Luke and Tyler take listeners behind the scenes as they run the full pro forma on the Kentucky bourbon‑trail property introduced in the previous episode. This is where the deal gets real — revenue assumptions, expense modeling, financing scenarios, and risk analysis all collide to reveal whether this property is a cash‑flowing gem or a pass.

If you’ve ever wondered how experienced STR investors turn raw market data into a confident investment decision, this episode is your blueprint.

• 🧮 How to build a complete STR pro forma using real comps, ADRs, and occupancy data
• 💸 Expense modeling that actually reflects reality, from utilities to CapEx
• 🏦 How financing structure impacts cash flow, DSCR, and long‑term returns
• 📈 How to translate market data into revenue projections you can defend
• 🧪 Stress‑testing the deal with conservative, base, and aggressive scenarios
• 🛋️ How design upgrades and amenities influence revenue potential
• 🔍 How to validate assumptions using calendar activity, reviews, and competitor performance
• 🚧 How to factor in regulation risk, seasonality, and local demand cycles
• 🔄 Backup strategies like mid‑term and long‑term rentals to protect your downside
• 🧠 How to decide whether to move forward, renegotiate, or walk away

#ShortTermRental #STRInvesting #RealEstateInvesting #AirbnbHost #AirbnbAnalysis #ProForma #Underwriting #CashFlow #AirDNA #STRInsights #BourbonTrail #KentuckyRealEstate #InvestmentProperty #RealEstatePodcast #STRStrategy #VacationRentalInvesting #DealAnalysis #CompsAnalysis #RentalProperty

Luke and Tyler take you inside their underwriting process as they break down a promising short‑term rental opportunity in Lawrenceburg, Kentucky—right in the heart of bourbon country. They dig into market data, analyze comps, and stress‑test the numbers to determine whether this property has real investment potential. This episode is packed with practical insights for both new investors and seasoned hosts looking to sharpen their analysis skills.

• 🔍 How to evaluate a property’s listing, photos, and features to spot strengths, weaknesses, and value‑add opportunities
• 📈 Why tools like AirDNA and STR Insights matter when analyzing markets and projecting performance
• 🧭 How to interpret submarket scores, ADRs, occupancy rates, and regulation factors to understand risk and demand
• 💰 Ways to estimate revenue ranges using multiple data sources for a more reliable underwriting model
• 🛋️ How amenities, design upgrades, and competitive positioning influence your earning potential
• 📅 How to verify data accuracy by checking calendars, booking patterns, and listing reviews
• 🔄 Backup strategies using long‑term and midterm rental options to protect your downside
• 🧮 How to build a strong comps set that reflects true market performance
• 🛠️ Which free and paid tools can support ongoing market research and smarter investment decisions

#ShortTermRental #STRInvesting #RealEstateInvesting #AirbnbHost #AirbnbInvesting #Underwriting #AirDNA #STRInsights #KentuckyBourbonTrail #RealEstateAnalysis #CashFlow #RentalProperty #PropertyInvesting #BourbonCountry #InvestingPodcast #RealEstatePodcast #STRStrategy #VacationRentalInvesting #MarketAnalysis #CompsAnalysis

In this episode, Luke and Tyler break down a real-world case study from a luxury short-term rental on 30A in Florida.

What started as a casual conversation at cheer practice turned into a full revenue turnaround. The property was generating roughly $63,000 annually before Luke stepped in to manage pricing and provide strategic consulting. With no major renovation and only minor amenity upgrades, the property increased to over $113,000 in the first year.

And here’s the kicker: as of late February, 2026 booked revenue has already exceeded the total revenue from 2025 — with peak summer still ahead.

So what changed?

Not complicated tactics. Not a $50,000 remodel.

Just nailing the fundamentals.

In this episode, Luke explains:

• Why revenue management must start with listing optimization
• How small upgrades (coffee station, dedicated workspace, fire table) can improve competitiveness
• When to be price-sensitive vs. occupancy-sensitive
• Why you should "go high" when market occupancy is above 75%
• Why you should "go low first" when market occupancy drops below 50%
• How shoulder season strategy can dramatically increase annual revenue
• Why improving occupancy increases reviews, ranking, and Airbnb visibility

The property now holds a Top 5% badge on Airbnb and is ranking on page one in its market.

This episode is also a reminder that loving your property isn’t enough. When you start thinking like a homeowner instead of an investor, blind spots form. Sometimes all it takes is an honest outside perspective to unlock another level of performance.

The fundamentals work — if you actually execute them.

00:00 – Introduction and Quick Win Overview
01:00 – How This 30A Relationship Started
04:00 – Listing Optimization Before Pricing
05:30 – The Jump from $63K to $113K
07:00 – Top 5% Airbnb Badge & Page One Ranking
08:00 – 2026 Bookings Already Surpassing 2025
09:15 – Conservative Revenue Projections
10:30 – Hospitality + Strategy = Results
11:40 – The Core Revenue Management Fundamentals
14:00 – Investor Hat vs. Homeowner Hat
15:00 – New Website Announcement

The information shared in this episode is for educational and informational purposes only. Revenue results discussed are specific to this property, market conditions, timing, and execution. Past performance does not guarantee future results. Always conduct your own due diligence and consult appropriate professionals before making investment or business decisions.